Thionyl Chloride → 1-methyl-1H-indazole-3-carbonyl chloride

HRID 618665Notes

Reaction equation

HRID 618665 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([OH:13])=O)=[N:3]1.S(Cl)([Cl:16])=O>CCOCC.CN(C)C=O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([Cl:16])=[O:13])=[N:3]1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 6891051H-Indazole-3-carboxylic acid, 1-methyl-

Product 1

HCID 70220551-methyl-1H-indazole-3-carbonyl chlorideYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 3283Diethyl EtherSolvent

Procedure

A stirred suspension of 1-methyl-indazole-3-carboxylic acid (0.68 g, 3.86 mol) in anhydrous ether (50 ml) was treated with thionyl chloride (0.28 ml, 3.84 mol) and a few drops of dimethylformamide. After stirring for one hour the solid dissolved. The solvent was evaporated to give 1-methyl-indazole-3-carbonyl chloride as a yellow solid (0.75 g, 100%).

Workup

  1. dissolutiondissolved
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-923295db56744aadb0630742fbec9dfe
Source dataset
uspto-grants-1999_09
Patent number
US05955470

Reaction notes

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